(2S,3R,6R)-2-[(R)-1-Hydroxyallyl]-4,4-dimethoxy-6-methyltetrahydro-2H-pyran-3-ol

被引：0
|
作者：
Bennett, Jack [1 ]
Murphy, Paul, V [1 ]
机构：
[1] Natl Univ Ireland, Sch Chem, Galway H91 TK33, Ireland
来源：
MOLBANK | 2020年 / 2020卷 / 02期
关键词：
glucose; tetrahydropyran; deprotection; cyclisation; functionalized scaffold;
D O I：
10.3390/M1140
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
(2S,3R,6R)-2-[(R)-1-Hydroxyallyl]-4,4-dimethoxy-6-methyltetrahydro-2H-pyran-3-ol was isolated in 18% after treating the glucose derived (5R,6S,7R)-5,6,7-tris[(triethylsilyl)oxy]nona-1,8-dien-4-one with (1S)-(+)-10-camphorsulfonic acid (CSA). The one-pot formation of the title compound involved triethylsilyl (TES) removal, alkene isomerization, intramolecular conjugate addition and ketal formation. The compound was characterized by(1)H and(13)C NMR spectroscopy, ESI mass spectrometry and IR spectroscopy. NMR spectroscopy was used to establish the product structure, including the conformation of its tetrahydropyran ring.
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页码：1 / 5
页数：5
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